Triethylamine → 2-[(R)-alpha-methoxy-alpha-trifluoromethylphenylacetylamino]-4-(4-octylphenyl)butanol

HRID 842280

반응식

HRID 842280 반응식
[NH2:1][CH:2]([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:8]=1)[CH2:3][OH:4].C(N(CC)CC)C.[CH3:28][O:29][C@:30]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:34]([F:37])([F:36])[F:35])[C:31](Cl)=[O:32]>C(Cl)Cl>[CH3:28][O:29][C@@:30]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:34]([F:37])([F:36])[F:35])[C:31]([NH:1][CH:2]([CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:11][CH:12]=1)[CH2:3][OH:4])=[O:32]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 3080792(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetyl chlorideHCID 100642062-Amino-4-(4-octylphenyl)butan-1-ol

생성물 1

HCID 701464362-[(R)-alpha-methoxy-alpha-trifluoromethylphenylacetylamino]-4-(4-octylphenyl)butanol

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-Amino-4-(4-octylphenyl)butanol (10 mg), N,N-dimethyl-p-aminopyridine (17.5 mg), anhydrous triethylamine (11.4 μl) and anhydrous methylene chloride (1 ml) were mixed and the mixture was stirred under a nitrogen atmosphere at room temperature. Thereto was added (R)-α-methoxy-α-trifluoromethylphenylacetyl chloride (16.8 μl) and the mixture was stirred at room temperature for 10 hours. The reaction mixture was concentrated under reduced pressure and the residue obtained was purified by thin layer chromatography (eluent; chloroform:methanol=9:1) to give the two diastereomer mixtures. Moreover, the mixture was purified by high performance liquid chromatography (eluent; methanol:water=88:12, flow rate; 8.0 ml /minute) to give the subject oily substance (9.8 mg) of 67.8 minutes at retention time and the subject oily substance (9.6 mg) of 71.6 minutes at retention time.

후처리

  1. stirringthe mixture was stirred at room temperature for 10 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue obtained
  4. customwas purified by thin layer chromatography (eluent; chloroform:methanol=9:1)
  5. customto give the two diastereomer mixtures
  6. customMoreover, the mixture was purified by high performance liquid chromatography (eluent; methanol:water=88:12, flow rate; 8.0 ml /minute)
  7. customto give the subject oily substance (9.8 mg) of 67.8 minutes at retention time
  8. customthe subject oily substance (9.6 mg) of 71.6 minutes

출처 및 근거

ORD 기록
ord-87dd6862c20c4ff9ad6582dd8128191d
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06372800B1

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